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| CAS No.: | 501-53-1 |
|---|---|
| Name: | Benzyl chloroformate |
| Article Data: | 53 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H7ClO2 |
| Molecular Weight: | 170.595 |
| Synonyms: | Benzyl chlorocarbonate;Benzyloxycarbonyl chloride;Benzylcarbonyl chloride;Z-Cl;Benzyl carbonochloridate;Carbobenzoxy chloride;Chloroformic acid, benzyl ester;Formic acid, chloro-, benzyl ester;Carbonochloridic acid, phenylmethyl ester;Benzyl Chlorofomate;n-Amyl chloroformate,n-pentyl chloroformate;CBZ-CL;Benzyl chloroformate (CBZ-Cl);Carboobenzoxy Chloride;Cbz-Cl (Carboobenzoxy Chloride); |
| EINECS: | 207-925-0 |
| Density: | 1.244 g/cm3 |
| Melting Point: | -20 °C |
| Boiling Point: | 223.984 °C at 760 mmHg |
| Flash Point: | 73.488 °C |
| Solubility: | Soluble in most organic solvents; usually use in water, dichloromethane, THF, ether or toluene |
| Appearance: | light yellow liquid |
| Hazard Symbols: |
 T,  C,  N,  F
|
| Risk Codes: | 45-20-34-48/22-50/53-67-65-63-48/20-11 |
| Safety: | 53-26-36/37/39-45-60-61-62-46 |
| Transport Information: | UN 2924 3/PG 2 |
| PSA: | 26.30000 |
| LogP: | 2.56200 |
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O-benzyl S-methyl carbonothioate
- 501-53-1
benzyl chloroformate
| Conditions | Yield |
|---|---|
| With sulfuryl dichloride at 0 - 20℃; for 1h; | 100% |
| With sulfuryl dichloride at 20℃; for 1h; | 72% |
| With sulfuryl dichloride at 0 - 20℃; for 1h; | 72% |
| Conditions | Yield |
|---|---|
| With pyridine In dichloromethane at -5 - 10℃; for 13h; Reagent/catalyst; Temperature; Solvent; | 99% |
| With pyridine In dichloromethane | 98% |
| With pyridine In dichloromethane | 98% |
- 110177-67-8
S-ethyl O-benzyl carbonothioate
- 501-53-1
benzyl chloroformate
| Conditions | Yield |
|---|---|
| With sulfuryl dichloride at 20℃; for 1h; | 81% |
| With sulfuryl dichloride at 0 - 20℃; for 1h; | 81% |
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; | 76% |
| Conditions | Yield |
|---|---|
| With toluene anfangs unter Kuehlung; | |
| at -8℃; | |
| With 2,3-Dimethylaniline |
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benzyl carbonochloridate
- 501-53-1
benzyl chloroformate
| Conditions | Yield |
|---|---|
| With thionyl chloride at 90℃; for 3h; | |
| With thionyl chloride for 6h; Chlorination; Heating; | |
| With thionyl chloride for 4h; Reflux; | |
| With thionyl chloride at 90℃; for 2h; |
| Conditions | Yield |
|---|---|
| With pyrographite In tetrahydrofuran at 20℃; for 1h; Condensation; | |
| With dmap In toluene at 20℃; for 24h; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1.1: sulfur; DBU / dimethylsulfoxide / 5 h / 20 °C / 760 Torr 1.2: 67 percent / dimethylsulfoxide / 1 h / 20 °C 2.1: 100 percent / SO2Cl2 / 1 h / 0 - 20 °C View Scheme |
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Thiocarbonic acid O-benzyl ester
- 501-53-1
benzyl chloroformate
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C / 750.06 Torr 2: 81 percent / sulfuryl chloride / 1 h / 0 - 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: 1.62 g / tetrahydrofuran / 16 h / 20 °C / 750.06 Torr 2: 72 percent / sulfuryl chloride / 1 h / 0 - 20 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: DBU / tetrahydrofuran / 1 h / 20 °C / 750.06 Torr 2: tetrahydrofuran / 2 h / 20 °C / 750.06 Torr 3: 81 percent / sulfuryl chloride / 1 h / 0 - 20 °C View Scheme | |
| Multi-step reaction with 3 steps 1: DBU / tetrahydrofuran / 1 h / 20 °C / 750.06 Torr 2: 1.62 g / tetrahydrofuran / 16 h / 20 °C / 750.06 Torr 3: 72 percent / sulfuryl chloride / 1 h / 0 - 20 °C View Scheme | |
| Multi-step reaction with 3 steps 1: sulfur; DBU / tetrahydrofuran / 6 h / 80 °C / 7500.6 Torr 2: tetrahydrofuran / 2 h / 20 °C / 750.06 Torr 3: 81 percent / sulfuryl chloride / 1 h / 0 - 20 °C View Scheme |
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Specification
The Benzyl chloroformate, with the CAS registry number 501-53-1, is also known as Carbonochloridic acid, phenylmethyl ester. It belongs to the product categories of Pharmaceutical Intermediates; Benzene derivatives; Amino Acid Derivatives; Aromatic Esters; Chloroformates; N-Protecting Reagents; Biochemistry; Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry; Cbz-Amino acid series. Its EINECS number is 207-925-0. This chemical's molecular formula is C8H7ClO2 and molecular weight is 170.59. What's more, its systematic name is Benzyl carbonochloridate. It should be sealed and stored in a ventilated and dry place. Its storage temperature is 2 - 8°C. This chemical is used in organic synthesis for the introduction of the carboxybenzyl (Cbz,Z) protecting group for amines. It is also a carcinogen.
Physical properties of Benzyl chloroformate are:
(1)ACD/LogP: 1.862; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.86; (4)ACD/LogD (pH 7.4): 1.86; (5)ACD/BCF (pH 5.5): 15.32; (6)ACD/BCF (pH 7.4): 15.32; (7)ACD/KOC (pH 5.5): 245.54; (8)ACD/KOC (pH 7.4): 245.54; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.531; (14)Molar Refractivity: 42.426 cm3; (15)Molar Volume: 137.118 cm3; (16)Polarizability: 16.819×10-24cm3; (17)Surface Tension: 41.04 dyne/cm; (18)Density: 1.244 g/cm3; (19)Flash Point: 73.488 °C; (20)Enthalpy of Vaporization: 46.048 kJ/mol; (21)Boiling Point: 223.984 °C at 760 mmHg; (22)Vapour Pressure: 0.093 mmHg at 25°C.
Preparation of Benzyl chloroformate:
This chemical can be prepared by phosgene and benzyl alcohol. The yield is about 91-94%. It can also be prepared by benzyl alcohol and trichloromethyl chloroformate. In laboratory, it can be prepared by benzyl alcohol and phosgene in the present of toluene.
Uses of Benzyl chloroformate:
It can be used to produce N-benzyloxycarbonyl-anthranilic acid at the ambient temperature. It will need reagent 1N NaOH and solvent dioxane. The yield is about 72%.
Safety information of Benzyl chloroformate:
When you are using Benzyl chloroformate, please be cautious about it as the following:This chemical is harmful as it has a danger of serious damage to health by prolonged exposure through inhalation or if swallowed. It is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environmen. Moreover, it may cause cancer. This substance is harmful by inhalation and is harmful as it may cause lung damage if swallowed. If swallowed, it will not induce vomiting, but you should seek medical advice immediately and show this container or label. It can cause burns and is highly flammable. It has a possible risk of harm to the unborn child. Its Vapours may cause drowsiness and dizziness. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible). It must be avoided exposure, and you need to obtain special instructions before use. This material and its container must be disposed of as hazardous waste. You should avoid releasing to the environment, and you need to refer to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: ClC(=O)OCc1ccccc1
(2)Std. InChI: InChI=1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2
(3)Std. InChIKey: HSDAJNMJOMSNEV-UHFFFAOYSA-N
The toxicity data of Benzyl chloroformate is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| rat | LC50 | inhalation | 590mg/m3/4H (590mg/m3) | National Technical Information Service. Vol. OTS0539682, | |
| rat | LD50 | oral | 3gm/kg (3000mg/kg) | National Technical Information Service. Vol. OTS0539682, |